Hydrochloric Acid → HCID 54054669, compound

HRID 987306Notes

Reaction equation

HRID 987306 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:15][C:16](=[O:38])[CH:17]([O:35][CH2:36][CH3:37])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:21][CH:20]=1)[CH3:14].Cl>ClCCl>[CH2:13]([O:15][C:16](=[O:38])[CH:17]([O:35][CH2:36][CH3:37])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([NH:34][S:9]([CH3:8])(=[O:11])=[O:10])=[CH:32][CH:33]=2)=[CH:21][CH:20]=1)[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53920635HCID 53920635, compound

Product 1

HCID 54054669HCID 54054669, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.544 g; 2.99 mmole) and thereafter methanesulfonyl chloride (0.392 g; 2.99 mmole) were added to a solution of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester (0.89 g; 2.49 mmole) in dichloromethane (8.9 ml) at 0° C. After stirring at room temperature for 20 hours the reaction mixture was poured onto a mixture of hydrochloric acid and ice. Dichloromethane was added, the phases were separated and the organic phase was washed with water, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. Purification by chromatography on silica gel using heptane:ethyl acetate (3:2) as eluant gave 0.78 g (yield 72%) of 2-ethoxy-3-{4-[2-(4-methanesulfonylaminophenyl)ethoxy]phenyl}propanoic acid ethyl ester.

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-0bd7edbde247463398aec250d160fa0d
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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